First is the Worst
by lostlikeme
Summary: The boys experience their firsts in no particular order or importance. 100-Word Snippets. Warning for explicit content.
1. Chapter 1

Cartman gives his first kiss to Butters, because he's sure he won't be rejected. Butters is as gay as they come: flamboyant, effeminate, and born to take it where the sun don't shine. Instead, his lips remain frozen and unmoving.

"What the fuck Butters? Haven't you ever kissed someone before? Goddamn."

Then Cartman realizes, of course not, because Butters is genuinely as naive as he appears. Cartman likes that about Butters.

"It sure is nice that you like me an' all. But Eric, I don't like boys."

Cartman's jaw drops.

"I won't tell nobody," Butters offers, like it's any consolation.


	2. Chapter 2

Kenny shares his first kiss with someone four years his junior, and all he can think about is the kid's older brother. He's wondering just how Kyle will kill him. He hopes that it's quick and painless.

He reels back almost immediately, feeling like shit and like he needs a beer.

"Hey," he says, trying to sound casual. It's definitely awkward.

"I already know," Ike cuts him short. Kenny doesn't understand how Ike could possibly know.

"Wait—" Kenny starts, stops. Unsure.

But Ike jumps over the side of Kenny's piece-of-shit-pickup before Kenny even has the chance to say, "Don't go."


	3. Chapter 3

Kyle's first kiss is stolen from him when he's five years old. It happens during nap time, and the press of someone's lips against his own wakes Kyle up immediately. He comes face to face with a girl with long, dark hair, and deep, dark eyes. She's wearing a purple hat and a smile like they're the only accessories she'll ever need.

Not sure what to make of the entire thing, Kyle decides to roll over and go back to sleep.

It isn't until fourth grade that Kyle realizes he's kissed Wendy Testaburger.

He decides to never, ever, tell Stan.


	4. Chapter 4

Stan's first kiss is with Wendy in the fourth grade, and it's her first kiss too, which is kind of gay but cool at the same time. Stan is so elated when she finally leans forward that he has to think about playing video games with Kyle and the sleepover that they're having later this week just to stop the bile from rising in his throat.

It's a slight peck, a firm press of lips, but Stan has never been more nervous in his life.

The kiss lasts the entirety of two and a half seconds, and afterward, Stanley vomits.


	5. Chapter 5

Stan blows his first load by mistake, two inches from Kyle at two o'clock in the morning. He sits straight up in bed and lifts the mauve comforter with shaking fingers, half afraid of finding a yellow stain spreading across the sheets. Instead his underwear is glued to skin, spunk-stuck to his thighs.

When Stan finally slips out of the coverlet Kyle cracks his eyes open. He doesn't interrupt until Stan begins pilfering a pair of Terrance and Phillip y-fronts from his top left drawer.

"Stan?" Kyle whispers worriedly into the darkness.

"I don't know what happened," Stan confesses miserably.


	6. Chapter 6

The first time Cartman comes into his own hand is the day he truly becomes a man. He's thinking about Kyle sucking his balls when it happens, one of his earliest and tamest fantasies. He can hear Leane enjoying her "gentleman company," through the paper thin walls. He pictures it without meaning to and shoots off like chinese gunpowder.

Spent, he exits 4chan, clears his browser history, and takes a cold shower. He entertains the thought of murdering the man in the other room, but settles for slashing his tires tomorrow if he still feels up for it after breakfast.


	7. Chapter 7

The first time Kenny busts a nut is better than Christmas in July, and he doesn't even have to share. He spread his legs in front of an outdated issue of Playboy magazine he nicked from his Dad's room and spends all afternoon reading the articles and jerking off.

It feels like sneezing straight from his dick, but in technicolor. Afterward he creates a cumsock named Charlie and hides him under the foot of his bed. It's not summertime but Kenny refuses to go to school for so long that everyone thinks he's dead again. Who's to say he isn't?


	8. Chapter 8

All manner of fat jokes aside, Cartman excels at eating pussy. The first time he does it is with Wendy, two weeks before the Big Breakup. She pulls his hair and calls him Stanley by mistake. It's not as finger lickin' good as KFC's gravy, but it's goddamn close.

She insists she'll cut him off if he doesn't curb his bad behavior, and Cartman believes her-the stingy bitch that she is. In the end, she's the one who ends up addicted; Cartman is the only one who can tongue her til she sets off like an unlocked fire hydrant.


	9. Chapter 9

Kenny offers Craig his virginity because having sex and liking the person aren't mutually exclusive. Craig Tucker is experienced, safe, and most importantly, bisexual.

"You have to bring your own condom," Craig reminds him in the hallway before lunch.

At his house, Craig works Kenny open with a contradiction of gentility and carelessness. He sinks into Kenny for the first time, cock wrapped tight like leftovers behind cellophane.

"You've done this before, haven't you?" he asks when he pulls back out.

Even without the sappy romance it shakes him like an electric current.

Kenny shakes his head. "Not with you."


	10. Chapter 10

Kyle gets blackout drunk for the first time the night before he's supposed to take the SATs. He tells Stan to go to hell, punches Cartman in the mouth, and vomits all over himself while palming his dick through his pants like a rapper.

"Dude," Stan stays.

Cartman won't stop laughing about the vomit chunks on Craig's front lawn.

"Dude," Kenny says. "This is why we never get invited to parties."

In the morning Kyle's eyes are bloodshot, his ears are ringing, and he almost misspells his last name twice. (He gets the second highest score in the school, anyway.)


	11. Chapter 11

"I don't get why we have to use a condom," Stan keeps saying.

"Yes you do," Kyle snaps, tearing it open. "I'm not gonna explain it again, Stan." Stan watches entranced as Kyle rolls the translucent latex onto his throbbing dick. "I can't believe this is the first time you've used one."

Kyle winces awhen Stan works his dick slowly inside him. When Stan hesitates Kyle tilts his hips.

"We can't stop now," he complains.

Stan bows his head, licks Kyle's neck, and thrusts into him in swift, sure movements. Kyle becomes placid, open, drooling. They fall asleep stuck together.


	12. Chapter 12

Kyle pops his first Ritalin the night before college finals. Ike tells him to take two with breakfast but Kyle is feeling adventurous so he takes three and spends the next sixteen hours cycling through Wikipedia pages about nuclear holocaust when he's supposed to be studying. It's as close to a k-hole as he'll ever come.

When he wakes up some immeasurable amount of time later, he can recall everything he read with startling clarity. Unfortunately, tests are over.

"This is why drugs are bad," he reminds Ike during break.

Ike scoffs. "Or maybe you're just bad at doing drugs."


	13. Chapter 13

Kenny knows how to give a blowjob, sure, but today he gets one of his very own. Kyle takes him to the root like a guy who's been sucking dick for at least four years and begs him not to tell Stan afterward. They haven't dated since they split for college, and Kenny is pretty sure Kyle is fucking Cartman at Yale - but Stan still posts lame poetry about his broken heart on Facebook so nobody talks about it.

"I knew you'd understand," Kyle says.

"I'm an understanding guy," Kenny says, before zipping up. "But I won't lie for you."


	14. Chapter 14

The first time Stan cheats on Kyle is the biggest mistake of his life. Kyle won't take him back and time doesn't mend the wound, not even with two thousand miles between them. He flunks out of community college and spends his mornings playing Guitar Hero drunk, even though he's not half as good as he was when he was a kid.

He's still crying that Tuesday night when Kenny comes over after his shift to watch reruns on Terrance and Phillip.

"Dude," Kenny says. "This is why we still don't get invited to Craig and Tweek's big gay parties."


	15. Chapter 15

Kyle fails a class for the first time because he can't stop thinking about Stan curled up in the fetal position and because his Psych teacher is a pretentious douchebag. He convinces Wendy to call Stan to give him peace of mind, and now they're back together instead, like some kind of perfect Barbie fairytale.

The entire dorm floor is blessedly, disturbing quiet on the way back to his room. He spies a familiar silhouette in the common area, inhaling cheesey poofs in front of Judge Judy. Looks like they didn't have room at the party for a Fatass, either.


	16. Chapter 16

Semen isn't the only thing Kyle sucks straight from Cartman's dick. A slew of feelings get funneled out through his urethra for the first time, this ugly thing that resembles affection, worse than he ever had it for Wendy or Butters. Apparently passive-aggressive Type-A personalities with no gag-reflex are his type.

Afterward, Kyle spits into the wastebasket and makes a face like he just sucked a lemon. He passes out diagonally across the mattress with all his clothes on, reeking of alcohol. Later that night, when he rolls over with the blanket wrapped around him, Cartman knows he's irreversibly fucked.


	17. Chapter 17

"Holy shit," Stan says. "I can't believe you're - we're - pregnant."

The wind chime on her front porch jingles, they can hear it from her tiny living room apartment. Wendy snatches the pregnancy test from Stan's fingers while he stares, dumbfounded, at the space it used to fill in his hands.

"This is negative, Stan."

It's impossible not to cry after that first pregnancy scare, for the dad he won't get a chance to be and their baby that never was. He feels behind, trudging through two credit courses while everyone else is graduating.

Maybe this is what they're working for.


	18. Chapter 18

Kyle has been blowing him on and off all semester since he failed intro to psych, and Eric wants to keep it that way. The first time he apologizes, he has that explicit purpose in mind.

"What was that?"

"I said…" Cartman puckers his lips and screws his eyes shut. "I'm sorry."

"Oh. Okay." The tension drains from Kyle's face like a deflated red balloon. "Apology accepted, I guess."

"Really? So you're not gonna…" Cartman sniffles dramatically. "Break up with meeeeee?"

"Over the hair in the bathroom sink?" Kyle falters, one hand braced on the headboard. "Are we going out?"


	19. Chapter 19

The first time Kenny says I love you is a mistake. Two months after he loses his job, Ike finds him at one of Craig's parties, slurping a forty on his mom's couch like a first-class loser. Ten minutes later, they're tonguing each other.

"I love you," Kenny slurs into his mouth.

"What?" says Ike.

"What?" echoes Kenny.

"What did you say?"

Ike is eighteen now, but it doesn't make the tension any easier to digest. Kenny swallows up his feelings and tries to laugh the whole thing off.

"I said I drugged you. I slipped roofies in your drink."


	20. Chapter 20

This is their first argument since they made it Facebook official, and it feels different, somehow. Weighted, heavier than all that stuff from when they were just kids. Cartman swallows.

"How do I know you care about me and this isn't part of your Jew scheme to get more Jew gold?"

"How do I know you really love me and this isn't the third step in a twenty-three step process to humiliate me and destroy my life?"

"Kahl, please." Cartman rolls his eyes. "I'd marry you."

"Seriously," Kyle says, face red. "I think we should at least live together first."


	21. Chapter 21

The first time Stan gets engaged he's on a date with Wendy at this shitty Italian place to celebrate his new job, because someone on Yelp called it an "unforgettable assault of the senses."

Wendy bends down after the waitress drops off their dessert, and Stan spends two full minutes wondering just what the hell she's doing before he notices her kneeling. She reaches into her pocket and produces a small box. Stan already knows what's inside, and he can't help tearing up.

"Oh," he says quietly. "I just thought you were taking a really long time tying your shoes."


	22. Chapter 22

Kyle gets married for the first time the night Stan and Wendy announce their engagement. He's on Spring Break in Florida with Cartman, and they've had at least four shots each. The whole thing starts off as a joke, spirals into a competition, and rollercoasters downhill from there.

"Stan has a lot of nerve," Kyle slurs into his drink. "He used to be gay."

"Yeah," says Cartman. "We'd be way better at being married than those heteronormative pieces of shit."

They exchange vows about fellatio and chores over two ring pops, and wake up full of regret in the morning.


	23. Chapter 23

Nobody really believes Cartman is serious about having his first kid until he shows up in South Park with an infant. Kyle is stuck hauling the diaper bag over his shoulder, complete with sixty different compartments, so he never knows which one has the pacifier.

"Look at little Fatass junior."

"Don't call my baby fat you poor piece of shit!"

Stan peers at the pink bundle in Cartman's arms incredulously.

"Are you sure she's not a boy, dude?"

"Excuse me?" Kyle snaps.

Cartman sniffs. "She has his vagina."

"I can't believe you really have a kid," Stan says. "On purpose."


	24. Chapter 24

In the end, it's all too weird. After everything Kenny has seen - heaven and hell, tits and balls, man, bear, pig, and everything in between - this is where he draws the line. Some of his friends are having kids. Ike moved away to college, and his sister is leaving come July. Everyone has started growing up, so why hasn't he?

He drinks in his truck and passes out in the back, alone under the the stars. He wakes up a couple hours later and starts driving, sobering up along the way.

This is the first time Kenny leaves South Park.


End file.
